When he was born
c. 985, there was no expectation Cynfyn would ever become a king. His ancestors had been among the leading men
of Powys for hundreds of years, but the kingdom had been ruled by another ancient family which was still in power. His
father had married the daughter, and only child, of King Cadell ap Brochwel II. But Cadell had brothers and nephews
eligible to rule after his death; seldom did a Welsh kingship descend through female lines, and never if their was an eligible
qualified male heir. But such a circumstance appears to have occurred
in 1023, when the existing king died (or was killed) fairly early in his life and at a time when both his son and other qualified
males in the Royal Family were too young for kingship. [1]

Cynfyn's father, Gwerystan
ap Gwaithfoed of Powys, was a great-grandson of Lles Llyddog, the warrior who led the early 10th century expedition to evict
a colony of Danes who had settled in North Wales. [2] He is sometimes called Lord of Cibwyr in Gwent [3], but his manor
was actually Cwybr near Rhuddlan in Tegeingl. Having descended from Lles Llyddog, it is possible Gwerystan served as
penteulu for King Cadell, particularly if an earlier marriage had made him the king's cousin:

855 Lles Llydog 850 Selyf I

l
l

885 Gwynnog 880 Aeddan II

_________l_____
l

l
l
l

915 Gwaithfoed 925
daughter(a)==Brochwel 910

l
l

l 940
Cadell

l
l

955 Gwerystan==============Nest
970

l

985 Cynfyn

(a) No wife
is anywhere cited for Brochwel, nor such a daughter for Gwynnog, but a marriage like the one charted would have made Gwerystan
a first-cousin of Cadell and eligible to lead the king's warband. As such, he may have been rewarded with the hand of
Cadell's only child...a marriage which IS cited in the sources [4]

Cynfyn
is known to have had a wife prior to his 1023 marriage to Angharad ferch Maredudd ap Owain, the widow of Powys king Llewelyn
ap Seisyll. We suggest the leading families of Gwynedd, Powys and Deheubarth were friends, and sometimes military
allies, of Sitric Silkbeard of Dublin during the period 990-1042. We know that his grandson, also called Sitric,
married a sister of Rhys ap Tewdwr of Deheubarth [5], and that his granddaughter, Rhanillt, married Cynan
ap Idwal of Gwynedd and was mother of the first Gruffudd ap Cynan.[6] And we know that in the year 1000, Irish king
Brian attacked Sitric Silkbeard and evicted him from Dublin...a defeat he overcame in 1014 by killing Brian and retaking Dublin. [7]
We suggest a young Cynfyn ap Gwerystan brought a group of Powys men to assist Sitric, and took home a daughter of that
Irish king as his wife:

920 Olaf Cuaran, ob 981

l

960 Sitric Silkbeard, ob 1042

___________________l________

l
l

1000 daughter
995 Olaf [8]

=
_________________l_________

985 Cynfyn ap
l l
l

Gwerystan
l l
l

1025 Nest 1026 Rhanillt 1030 Sitric

= = =

1011 Gruffudd 1014 Cynan 1045 Nest

ap ap ferch

Llewelyn Idwal Tewdwr

NOTES:
The name "Sitric" is also rendered "Sigtrygg" and "Olaf" as "Afloed". The marriage shown for Cynfyn is only a guess
and nowhere cited, as is the marriage for Gruffudd ap Llewelyn. Several early sources match Rhanillt with Cynan but
call him Cynan ap Iago, a later man born c. 1035. This Cynan was an older brother of Iago. The final marriage
in our chart is also cited by several sources; Sitric and Nest ferch Tewdwr ap Cadell were the parents of Eidio Wyllt.

It appears
that Cynfyn and the Irish princess had three daughters, and that she probably did not survive her final childbirth.
These daughters were:

a. Efa, born
c. 1018, who married Llewelyn ap Coel [9], the man later chosen as penteulu for King Gruffudd ap Llewelyn and thereafter known
as Llewelyn Aurdorchog.

b. Nest, born
c. 1020, who married Ithel ap Coel, brother of Llewelyn, and who probably served Gruffudd ap Llewelyn as trainer and handler
of the Royal hunting hounds. [10]

c. Iwerydd,
born c. 1022. This was likely not her birthname, but a nickname to denote her Irish mother, who may have died during
this birth. She was given in marriage to Edwin of Tegeingl [11] about 1050, but probably had a first unknown
husband.

When Powys
King Llewelyn ap Seisyll died, or was killed, in 1023, we suggest Cynfyn was named interim king during the minority of the
young heir, Gruffudd ap Llewelyn...then about 12 years old. It may have been a condition of that appointment that Cynfyn
marry the widow of Llewelyn and become the step-father of the future king. He did marry Angharad, and together they
had 3 known children:

a. Rhiwallon,
born c. 1024, who was elevated to king of Powys after the death of Gruffudd ap Llewelyn

b. Bleddyn,
born c. 1025, who was made king of Gwynedd after Gruffudd's death in 1063, and additionally king of Powys when Rhiwallon was
killed in 1069

c. Unnamed
daughter, born c. 1026, who married Gwrgan ap Ithel of Glamorgan, and was mother to Iestyn ap Gwrgan. [12]

For the first
10 years of his reign, Powys is not mentioned in Brut entries, the conclusion being that there was neither internal unrest
nor conflicts with neighboring kingdoms. It is likely that Cynfyn was a caretaker monarch who refrained from making
waves. The picture is less clear after 1033. Iago ap Idwal of Gwynedd came of full age and now held its kingship.
Did Cynfyn agree to step aside for Iago or was it necessary for the Gwynedd heir to take his birthright by force? That
question is not answered directly by the Brut chronicler, but there is reason to suggest Powys and Gwynedd were on friendly
terms in 1033. Not only was Iago elected king of Gwynedd, but he was given a Powys lady for his wife [13]:

915
Cynwrig (a)

915 Meurig (b)
_____l_______

l
l l

945 Elisedd 950
Pyll Gweirydd 945

l
l l

975 Idwal 985
Gwyar Coel (c) 975

l
l l

1005
Iago==============Afandreg Llewelyn 1005

1020 (d)

(a) son of Cynddelw Gam ap Elgudy, the Powys warrior who aided Lles Llyddog in expelling the Danish squatters from northeast
Wales

(b) son of Idwal Foel ap Anarawd, king of Gwynedd

(c) married a sister of King Llewelyn ap Seisyll of Powys and Gwynedd

(d) led the warband of King Gruffudd ap Llewelyn after 1039 and was called Aurdorchog (with the gold torque).
About the same year of Iago's marriage, Llewelyn married the eldest daughter of Cynfyn of Powys

The estimated ages of Iago and Afandreg also point to the year 1033 as the date they were married. The Powys heir, Gruffudd
ap Llewelyn, was about age 21 and still waiting to attain "full" age when he'd be eligible for kingship. His time arrived
in 1039, and we think Cynfyn stepped down so Gruffudd could take his rightful place as king of Powys. It isn't known
if Gruffudd had developed a personal dislike for Iago, or if he simply believed Gwynedd belonged to him since his father had
ruled it. But Gruffudd's first recorded act as king was to kill Iago and seize Gwynedd. Others have speculated
that Iago may have been complicit in the death of Llewelyn ap Seisyll, and Gruffudd was simply taking his revenge. We
think Iago was only a teenager when Llewelyn died and doubt that he, or anyone from Gwynedd, killed him.

If we were to posit
a scenerio in which Gruffudd ap Llewelyn had a personal animus against Iago, it would develop along the following lines:

If Cynfyn had refused
to quit the throne of Gwynedd when Iago came of age in 1033, Iago might have battled for his birthright and killed Cynfyn.
Among the Powys barons who may have also died supporting Cynfyn was Gwyar ap Pyll, whose daughter Iago captured and took as
his wife. The remainder of the Powys royal family fled to Ireland for their safety where Gruffudd ap Llewelyn and his
entourage were given refuge by Sitric Silkbeard. That Irish king, about 1039, gave his eldest grand-daughter as wife
for the Powys heir, and troops to support Gruffudd's return to Wales. After being confirmed as the new king of Powys,
his first order of business was to kill Iago and seize Gwynedd, both to revenge his step-father Cynfyn and to restore rule
over Gwynedd which his father had held.

We are not told
when Cynfyn died nor in what manner, so no one really knows whether Iago's killing broke an extended period of peace between
Powys and Gwynedd or if Iago had earlier warred against Powys. The only reason to suspect the Powys royalty had to flee
to Ireland is the oral tradition that the first wife of Gruffudd ap Llewelyn was an Irish lady [14].

NOTES:

[1] A chart showing the men of the Powys Royal Family living in 1023 is shown
in the paper "The 1039 Battle at Rhyd y Groes" elsewhere on this site

[2] See the paper "The Retaking of Northeast Wales" elsewhere on this site

[3] This error in the residence of Cynfyn was first published in Iolo Morganwg's
forgery now called the Gwentian Brut; an English language version of that fake Brut was published at the end of the 1864
edition of Archaeologia Cambrensis

[4] Dwnn i, 310, 319, 326; Dwnn ii, 54, 249

[5] Dwnn i, 224

[6] Refer to the paper "Gruffudd ap Cynan - A New Perspective" under "The Royal
Family of Gwynedd" elsewhere on this site